Propiolic acid
| Propiolic acid | ||
|---|---|---|
 | ||
 | ||
| IUPAC name 2-Propynoic acid | ||
| Other names Acetylene carboxylic acid, Propargylic acid, 'acetylene mono-carboxylic acid | ||
| Identifiers | ||
| CAS number | 471-25-0  | |
| ChEMBL | CHEMBL1213530  | |
| Jmol-3D images | Image 1 | |
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| Properties | ||
| Molecular formula | C3H2O2 | |
| Molar mass | 70.05 g/mol | |
| Density | 1.1325 g/cm3 | |
| Melting point | 9 °C | |
| Boiling point | 144 °C (decomp.) | |
| Hazards | ||
| MSDS | External MSDS | |
| EU classification |  T+ | |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | ||
| Infobox references | ||
Propiolic acid is an unsaturated carboxylic acid. It is a colourless liquid that crystallises to give silky crystals. Near its boiling point, it decomposes. It is soluble in water and possesses an odor like that of acetic acid.[1]
Preparation
It is prepared commercially by oxidizing propargyl alcohol at a lead electrode.[2] It can also be prepared by decarboxylation of acetylenedicarboxylic acid.
Reactions and applications
Exposure to sunlight converts it into trimesic acid (benzene-1,3,5-tricarboxylic acid). It undergoes bromination to give dibromoacrylic acid. With hydrogen chloride it forms chloroacrylic acid. Its ethyl ester condenses with hydrazine to form pyrazolone.
It forms a characteristic explosive solid upon treatment to its aqueous solution with ammoniacal silver nitrate. An amorphous explosive precipitate forms with ammoniacal cuprous chloride.
References
- ↑ ed, Susan Budavari, (1990). The Merck index an encyclopedia of chemicals, drugs, and biologicals (11. ed., 2. print. ed.). Rahway, NJ: Merck. pp. 7833,1911. ISBN 9780911910285.
- ↑ Wilhelm Riemenschneider “Carboxylic Acids, Aliphatic” Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a05_235.
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This article incorporates text from a publication now in the public domain: Chisholm, Hugh, ed. (1911). Encyclopædia Britannica (11th ed.). Cambridge University Press